T. Michael Cafagno, holds a Golden Band Davidoff Best Performance 2012 cigar at his store Tobacconnist of Greenwich Thursday, Aug. 16, 2012. The Tobacconist of Greenwich LTD won a national award called the Golden Band Davidoff Best Performance Award. less

T. Michael Cafagno, holds a Golden Band Davidoff Best Performance 2012 cigar at his store Tobacconnist of Greenwich Thursday, Aug. 16, 2012. The Tobacconist of Greenwich LTD won a national award called the ... more

The Tobacconist of Greenwich at 8 Havemeyer Place, Thursday Aug. 16, 2012. T. Michael Cafagno, owner of the Tobacconist of Greenwich LTD won a national award called the Golden Band Davidoff Best Performance Award. less

The Tobacconist of Greenwich at 8 Havemeyer Place, Thursday Aug. 16, 2012. T. Michael Cafagno, owner of the Tobacconist of Greenwich LTD won a national award called the Golden Band Davidoff Best Performance ... more

Michael Cafagno was directionless at age 19 in 2006 when he wandered into The Tobacconist of Greenwich, he said, and did something that most people would consider foolish. He spent about $500 -- more than he earned in a week as a waiter, on cigars.

It was actually a fortuitous move that changed the course of his career and life. Original owner Jimmy Lacerra, who opened The Tobacconist in 1974, recognized Cafagno's potential and told him, "Kid, come back in a week and I'll teach you what you're smoking."

Cafagno did return. "I came here almost every day. I fell in love with this place. Jimmy took me under his wing," said Cafagno, now the owner of the high-end smoke shop at 8 Havemeyer Place near Greenwich Avenue. The Tobacconist has a 150-square-foot walk-in humidor and sells about 200 kinds of cigars ranging from $7 to $45 each, as well as pipe tobacco, humidors, pipes and other smoking accessories.

Cafagno put his own stamp on the business, launching a website in 2009 and adding sophisticated marketing events including fundraisers for the Transportation Association of Greenwich. Those events coupled, with his status as merchant who had the most Davidoff Brand purchases in a calendar year in the U.S., earned Cafagno the Davidoff Golden Band Best Performance Award this month. The award means his shop is one of only six places worldwide to sell Davidoff's Golden Band cigars.

Cafagno has also maintained the traditions of Lacerra, who died in June 2011. Smoke, the music of the Rat Pack and conversation fill the shop, and he has continued the Friday Night Club where about 20 guys stop by to "smoke, drink and eat." One customer came from California to experience it.

Few customers come in just to buy. Many sit and relax in the leather couches and chairs. "This is like home. It's not like a retail store," said Cafagno, adding that he considers all customers the same when they walk through the door, whether they are captains of industry, celebrities or blue-collar workers.

"It's a great place to socialize with friends, meet new people, make connections and smoke cigars," said Jesse Freedman, of Mount Kisco, N.Y., a customer and friend.